Tom breaks the rules! (Part 3)

Play time was over, it was time to return to the very serious business of disciplining Tom. I gathered myself together and walked over to the sofa and sat down in the centre of it.

‘I know your certificate says you must be over the arm of the sofa for each spanking but I prefer to do OTK for a hand spanking. It’s much more personal and the connection between spanker and spankee is much stronger for it, so Tom, assume the position please.’

I patted my knee as he lifted his head up to look at me. He scrambled backwards to get to his feet and tried to step out of his jeans which were bunched around his ankles.

‘Oh no, they stay on, shuffling is so humiliating isn’t it? Come on, over my knee right now!’ I was grinning at him now because his face was suffused with embarrassed colour again. It really was humiliating for him to have to waddle like a duck every time he was asked to move.

‘Please Ma’am… I have a request.’ Tom’s eyes were down cast as he spoke.

‘Okay, but make it quick, we have a lot to get through this afternoon.’ I wanted him over my knee.

‘Please may I go to the bathroom? I need to pee so bad right now…’ His face was livid with colour and he sounded like a small child who couldn’t hold it any longer and just had to go!

‘I smiled, a big wide smile, ‘of course you can Tom, I shall lead the way.’

I stood and took hold of his cock and led him shuffling across the room and up the stairs. It was a painfully (for Tom) slow process, and my hand pumped his cock with each step we took. I was openly giggling at his predicament as he grunted and moaned his way up stairs. Never have 13 steps taken so long to climb. Finally we were at the bathroom and I led him in.

I stood back and watched as he lifted the seat and took hold of his rigid cock. He glanced over his shoulder to see if I was still there and I could tell he was desperately disappointed to find I was watching him very closely.

‘Get on with it Tom, and do not think for a moment you can shoot your load down the toilet.’ My voice was very stern.

‘Yes Ma’am, sorry Ma’am.’ He mumbled as his pee trickled out of his rigid cock.

I moved up behind him as he tried to pee with me watching. Apparently he was struggling to let it go. I decided to help him. I reached between his thighs and began to stroke his balls, he jerked forward and shot a terrified look at me over his shoulder.

Please Ma’am, please don’t… You’re gonna make me cum… I can’t hold on much longer…’

Oh Tom darling, are you telling me what I can and can’t do? You have your orders from Graham, nowhere in those orders did he intimate this would be an easy task for you.’ By now my hand was cupping and squeezing his balls and my fingers were massaging the base of his cock. I know, I know, I’m evil… get over it! I was having FUN!

He dropped forward and braced his hands against the wall in front of him groaning, he threw himself into the rhythm and began thrusting quickly, he grunted loudly and a stream of hot cum shot from his cock in a wide arc, completely missing the pan and hitting the front of the cistern.

Then he pee’d. A long steady stream of pee and the look of relief on his face was immense.

It wouldn’t be there for long…

I left him in the bathroom cleaning up his mess and went back downstairs, I texted Graham and asked him what punishment he had put in place for Tom breaking the orgasm rule. I was very honest and admitted my role in the breaking of the rule because it wasn’t fair to just blame Tom.

I got a text back immediately from him telling me to check my email. I clicked on my emails and found Graham’s response.

‘Hi, see attachment for Tom’s punishment. Sounds like you’re having fun with him! Maybe you could keep him for a night for me? Leo and I are heading off to Blackpool for a festival. I don’t think it’s a good idea to leave Tom to his own devices and he certainly wouldn’t want to traipse around all the gay bars with the two of us. Besides, I’m sure you could put him to good use? Let me know soonest darling so I can make firm arrangements. x’

~Random Punishment Selector~

Punishment Certificate. This certificate dictates that Tom, for the reason of breaking the no orgasm rule will receive the following punishment. Four sets of spankings. Set One: 320 swats with a clothes brush and Tom bending over the arm of the sofa Set Two: 490 swats with a Jokari Paddle and Tom bending over the arm of the sofa Set Three: 200 swats with a hairbrush and Tom bending over the arm of the sofa Set Four:  38 strokes with a cane and Tom bending over the arm of the sofa. These spankings will be carried out with Tom completely naked. In addition, Tom will receive the following extra punishments:  55 minutes of corner time or 11 x 5 minute sets.  3 x 4 minute sessions with a ginger fig inserted.  10 days of bedtime spankings (a minimum of 100 spanks to a maximum of 300 spanks each night.) A coating of “Tiger Balm”, “Icy Hot” or “Chilli heat” rubbed into Tom’s bottom and thighs at the end of each spanking, including bedtime spankings. this punishment will be carried out by Gemma. Failure to comply with the punishment will result in the above amounts being doubled and carried out by Graham. Signed: Graham cc: Gemma.

I shivered. Jeez that was a lot of spanking and caning! Not to mention 3 lots of 4 minutes with a ginger fig stuck up his arse! That stuff burned like crazy. To date, Graham had only insisted on that punishment for me once, and it was only for 1 minute. That was enough. Never again!

To be fair though I now had the rest of today and all of tomorrow and one whole night to be able to pull this off so it wasn’t beyond the realms of possibility that Tom could take Gray’s entire punishment and also finish mine off from earlier too! Plus, I wasn’t in trouble with Graham for making Tom break the rules! YAY!

Decision made, I emailed Graham back and told him Tom was fine with me for an overnight and tomorrow day. It also gave me a damn good excuse for cancelling June. I was babysitting a 38 year old naughty boy! I sent the email as Tom entered the room, and I was printing off the certificate. He immediately began to apologise to me. ‘I am so very sorry, it won’t happen again Ma’am I promise you, it was just too much… I couldn’t hold on any longer…’

I raised my eyebrow at his stammered explanation and without a word I handed him the certificate. He took it from me and began to read. His face paled considerably the lower down the certificate he got. Then he looked confused, ‘Ma’am, what is a ginger fig?’

I explained to him that a piece of very fresh ginger would be peeled and inserted into his ass. He looked even more confused, but not worried. He should have looked worried. I decided that he could find out for himself why it was deemed a fitting punishment.

‘Oh dear Tom, you really have landed yourself in hot water with your antics upstairs, time to take your punishment. Over the arm of the sofa and spread your legs. NOW.’ I barked the order out at him and he jumped and stared like a rabbit caught in the head lights.

‘I thought we were doing over the knee Ma’am?’ He managed to squeak out.

‘Which part of NOW did you not understand?’ I grabbed him by his limp cock and pulled him over to the sofa arm. He stumbled behind me with his jeans still around his ankles. He hurriedly bent over the sofa arm and spread his legs as wide as his jeans would allow. I left him there while I went to the kitchen to prepare 1 of the ginger figs. Jesus, three of these were going to burn like crazy, it was dripping with ginger juices!

I walked back into the lounge and stepped up behind him, ‘do not move out of position for any reason whatsoever Thomas, you are now under Graham’s punishment regime, not mine. If you move an inch he will assume you have failed to comply with his orders. Everything on the certificate will be doubled immediately and Graham will come over and carry out the entire punishment. Do I make myself clear?’ I would inform him of the change of plans for him later.

Yes Ma’am, very clear.’ His manner was now very subdued.

I ran my fingers over his very red and sore bottom. I split his cheeks and found his tight little sphincter winking at me. He jumped and was trying to clench everything all at once. I pulled on a disposable glove and then lubed up my finger before inserting it very slowly into his arse. He bucked as he felt it invade what appeared to be virgin space! Good, this was going to be even more humiliating for him. I withdrew my finger to the tip and then pushed it in moving it back and forth for a few minutes, pressing against his prostate gland until he was moaning into the cushion. I ran my other hand down between his legs and fondled his balls for a moment before moving forward to stroke his very hard cock. It would appear our Tom was not adverse to some anal play. I removed my finger from his hole and picked up the piece of the ginger.

‘Keep very still Tom, this is going to sting a little.’ I thought I should downplay it, I didn’t want him him panicking before it was in place. I pushed the long thin piece of ginger almost all the way in until there was hardly any left outside. ‘Tighten up around it for me please. Squeeze it, hard.’

He did and then he squealed like a stuck pig, his arse tried to push it out and he hopped from one foot to the other, squawking and crying and grunting.

I stood back and watched him for a little while with a smile on my face. I knew what this felt like and no words can describe that burning sensation adequately. I looked at my watch. ‘You have 4 minutes to go Thomas, be a dear and stop making so much noise.’

I stepped forward and crouched down to have a look at the effect the ginger fig had had on his erection. It was flaccid. I smiled. Graham certainly knew a thing or two about controlling male urges.

I gave the ginger fig a little twist, Tom was howling now and sobbing and squealing each time he clenched his arse as more ginger juice seeped in.

I sat down behind him and chuckled at the little dance he was performing. I also noted that his cock was erect again, ginger fig or not there was no stopping him! ! He really was an absolute delight. I couldn’t wait for later.

I decided to let him in on the change of plans after the first set of 4 minutes with the ginger had finished and I was removing it.

‘Oh, by the way Tom, Graham has told me to keep you tonight and tomorrow, given the length of time it’s going to take to complete both punishment certificates, we are going to have to work very hard indeed to squeeze it all in so I’ve decided to do all of the spanking tomorrow, start fresh as a daisy first thing in the morning and keep spanking set after set until they’re done. We can concentrate on the corner time and ginger punishments tonight and you will have your first bed time spanking as well, I also need to apply chilli heat to your bottom and thighs as per Graham’s instructions. Suck it up buttercup, this is going to burn!’

I pulled on a pair of disposable gloves and liberally applied a coating of chilli heat to Tom’s very sore bottom and overheated thighs and then because I apparently have a real evil streak in me, I rubbed it in really well.

He positively HOWLED, as that chilli heat set in properly. Jesus that stuff burns! Real tears streamed down his face and he sobbed as I led him across the room to what I now refer to as Tom’s naughty corner for 20 minutes corner time.

As before, I made Tom kneel down on the floor facing me with his hands on his head and his cock standing to attention like a good soldier should! Oh my goodness, it really was a magnificent sight. I leaned down and stroked his cock a little before ‘remembering’ I still had on my disposable gloves… that were loaded up with chilli heat cream … oops…

Did I mention Tom can HOWL and SQUEAL at the same time? I did justify my action quite simply. He had been told not to cum and he had broken the rules, now he was suffering the consequences of his actions.

Despite all of this, Tom’s cock remained rock solid and he never went anywhere close to his safe word. He took his punishment like a trooper. I was very pleased with him and once he was allowed out of the corner I allowed him to sit with me for a while and cuddle as I explained to him that it was all for his own good, and that while these were hard lessons he was learning all at once, he would learn them very well indeed.

He was listening quietly as I massaged cold cream into his cock and balls and over his bottom and thighs. His cock was now ramrod straight again and I was going to have some fun.

‘Has all the nasty heat gone away now Tom?’ I asked nicely.

Tom muttered… ‘Yes Ma’am’ in a very quiet voice.

‘Good. I have a pussy that requires your immediate attention. Step to it.’

And he did… for hours…